


Love Hurts

by TammyRenH



Series: Masquerade fills [4]
Category: Supernatural
Genre: Barbed Penis, Bottom Sam, Coming Untouched, Love Conquers All, M/M, Painful Sex, Werecats, including barbed cocks, kitty Dean
Language: English
Status: Completed
Published: 2020-04-18
Updated: 2020-04-18
Packaged: 2021-03-02 04:00:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,002
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23708773
Author URL: https://archiveofourown.org/users/TammyRenH/pseuds/TammyRenH
Summary: Written for the following masquerade prompt:  Dean gets cursed/turned into a werecat. They don't realize he's got a barbed penis too until they're in the middle of a certain delicate moment.The surprising part wasn’t that Dean ticked off a witch. Other than for his “Samwitch”, his feelings for witches had never changed. The real surprising part was that nothing like this had happened until now
Relationships: Dean Winchester/Sam Winchester
Series: Masquerade fills [4]
Series URL: https://archiveofourown.org/series/1701883
Comments: 6
Kudos: 222





	Love Hurts

**Author's Note:**

> Fourth and final masquerade fill. Sorry Sam for the ouchie!

The surprising part wasn’t that Dean ticked off a witch. Other than for his “Samwitch”, his feelings for witches had never changed. The real surprising was that nothing like this had happened until now. They had been working a case in a tiny town in Wisconsin, where several men had inexplicably disappeared. The only thing the men had in common, except for living in Cavil, population as of last census all of 2,222, was that they had been in a rocky relationship before they vanished. The partners left behind – five women and one man – didn’t seem all that mournful about their significant others’ disappearances, but maybe that was because they were being consoled by their newly acquired pets – 2 had dogs, 2 had cats, and one a hamster.  
  
The hunt led them to the manager of the local Dollar General – a woman in her late forties named Amy Winston who had a real chip on her shoulder concerning men – and especially for Dean who had tried to be suave and charming when he was first attempting to pry information from her. It took one glance around her office, located in the back of the store, for Sam to realize what she was and rush out to warn Dean. But it was too late, Dean was gone and in his place was a large tawny cat with brown stripes and really pissed off green eyes.  
  
Sam took Amy out of the store and had a long one on one, kinda witch to witch, conversation with her. Afterwards all the men were restored back including Dean – except Dean didn’t lose his ability to turn into a cat. As it turned out, once he figured out how to turn, Dean kind of liked being a cat from time to time. He was big for a cat, not tiger size but big enough when he sat in Sam’s lap – like he was doing now – he filled Sam’s entire lap and could easily reach Sam’s chin with his scratchy tongue. He refused to eat cat food in cat form, and when Sam jokingly mentioned getting him a collar Dean’s response was that considering their relationship, if anyone was going to wear a collar it would be Sam which, okay, fair. Dean was so content in his cat form that Sam stopped looking for a counter spell and just accepted that now and then, Dean was simply a cat.  
  
When he returned to his human form, Dean looked no different. No cat ears, no cat tongue, nothing had changed except well – Dean before the cat thing happened was protective and possessive as hell about Sam, Dean after was a whole another level of “this boy is mine.”  
  
Case in point, they had gone to the bar the night before. A man Sam was acquainted with, who shared his love (fetish according to Dean) of true crime, had asked Sam if he had been listening to “The Vanished” podcast, they were deep into their discussion when a hand grabbed Kenneth’s arm and pulled him away.  
  
“Ever hear of a little thing called personal space?” Dean asked Kenneth as he slipped an arm around Sam’s waist. Sam looked apologetically at Kenneth as Dean pressed him closer. “You were standing so close to him; your spit was hitting his chest.”  
  
“First of all – ew Dean.” Sam said, trying to squirm away from Dean but his brother just held on tighter. “Second, I’m sorry Kenneth, Dean is just a bit – “  
  
“Tired,” Dean interjected. “Sorry man, me and the big guy gotta run but hey good to see you again or whatever.”  
  
And with that, Sam was propelled out of the bar and into the parking lot. He had been ready to end the conversation anyway, had been ready five minutes before, but no way was he telling Dean that so instead he got into his side of the car, made sure Dean had a good look at his bitch face before saying “You should have just switched into cat form and spayed me.”  
  
“Good idea.” Dean said unrepentantly as he started the car. “Next time I will do just that.”Sam wouldn’t put it past him.

It had been 2 weeks since the change. Cas and Jack had gotten used to Dean in cat form – as long as Dean remembered to change back into human form when he wasn’t around them. The previous Friday, Dean had been so excited about the Chinese food Sam had brought home than he had changed in front of Jack, all 6’1” inch of his naked body on full display. Dean hadn’t been particularly bothered, just grabbed a box of Mongolian beef and began digging in, but Jack insisted he was permanently emotionally scarred from the experience.  
  
Cas and Jack had left early that morning to meet a few rogue angels who might have a way to bind Chuck, and since there was no word on where Chuck was, Sam was scouring his laptop for possible hunts while Dean-as-cat was sitting in his lap. Dean would rather swallow his tongue than confess in either form, but he liked it when Sam scratched behind his ears, and Sam was quickly becoming addicted to the sound of Dean purring. It was a deep sound, soothing, and the more Sam scratched the more the sound emanated from Dean.  
  
For several minutes, they sat like that until Dean apparently became bored and started shifting around in Sam’s lap.  
  
And oh yeah – it had been a while because the pressure Dean was putting on his cock was – yeah.  
  
Dean must have noticed, well of course he did, because his tail began to move, lazily rubbing a pattern on Sam’s upper thighs.  
  
Dean could understand Sam in this form, he was still 100% Dean, just unable to talk and furrier than normal. “Too bad you don’t still have that tail when you switch.” Sam said to him as he put down the laptop. “Think of the fun we could have.”  
  
Dean hissed and dug his claws into Sam’s legs which caused Sam to hiss in response. Then Dean-as-cat jumped off Sam’s lap – as graceful as you please - and landed as Dean.  
  
Dean was already more than half hard. Come to think of it, so was Sam.  
  
“It’s been a while….” Dean began, his hands roaming over his own chest brazenly, one stopping to pluck at a nipple.  
  
Sam was already standing up. “Meet you in the bedroom in five.”  
  
Sam had his own bedroom, Dean has his. But the bunker was a big place, and they found a room that looked forsaken and untaken care of on the outside, but inside they had installed a king-sized bed, and a dresser filled with lube, panties, and sex toys. Sam made his rounds, secured the bunker, and then found Dean there, lying on the bed, stroking his cock.  
  
Fifteen minutes later Sam was the one lying on his back on the huge bed with the memory foam mattress and the luxuriously soft sheets with his knees pulled up to his chest and Dean had three fingers inside of him.  
  
“Dean.” Sam said with a definite-not-whine. “I’m ready.”  
  
His cock was long, hard and dripping precome like it was trying to break a record. Dean’s cock wasn’t in any better shape, judging by the looks of it.  
  
“Gotta make sure you are stretched enough.” Dean smirked, fingers twisting inside of Sam. “It’s been a few weeks and I’m a lot to handle.”  
  
Sam managed to roll his eyes at the same time his back arched off the bed after Dean pushed on his sweet spot. “We could get the measuring tape out like we did when we were teenagers.”

But the thing was – Dean’s cock did look bigger. Not as big as Sam’s natch, and maybe not longer – but wider, more – substantial. Maybe Sam’s imagination was running away from him, it had really been too long.  
  
“Just stick it in already.” Sam grumbled, squeezing his ass cheeks together in a way that he hoped indicated he meant business. He felt Dean’s fingers clench deep inside him.  
  
“Such a sweet talker.” Dean teased, but thankfully removed his fingers, used the last of the lube in that particular tube (there were plenty others) to coat his cock before pushing inside Sam.  
  
Dean took it slow; he was always careful with Sam no matter how many times Sam groused that he wasn’t made of china, sure as hell wasn’t delicate, and would not break. Sam was appreciative of the carefulness this time though, because the burn was already intense, and Dean hadn’t gotten even a third of a way in.  
  
“You okay?” Dean asked, looking down at Sam, holding himself still.  
  
Sam nodded, taking deep breaths to push away the feeling of being too-full, of too-much. “Yeah, just, slow okay?”  
  
“Anything for you baby brother.” Dean continued to push in, Sam continued to try to relax through the burn. It hadn’t felt like this in years, not since they had first hooked up after Stanford.  
  
When Dean was in all the way he groaned and stilled. Sam was sweating, he could feel unwanted tears forming at the corner of his eyes. He blinked them away and closed his eyes, concentrating on how good it felt to have Dean inside of him again, allowing the burning feeling to begin to dissipate.  
  
It took longer than it normally did, but it wasn’t like they were in a rush, for Sam to finally nod his okay for Dean to start moving.  
  
Something was different, definitely different. The burning feeling was back with a vengeance and instead of it fading into pleasure like it normally did, it was intensifying into something akin to pain. Dean’s cock felt like sandpaper scraping his insides, even the pressure on his prostate didn’t feel good.  
  
Dean continue to push in, short, shallow thrusts. It was almost as if Dean’s cock was growing inside of him and there was something forming, something like –  
  
“Fuck, those are barbs!”  
  
“What?” Dean asked, still thrusting in.  
  
Sam grabbed his arms. “Stop. Fucking. Moving.”  
  
There were more tears that Sam had to blink through to see Dean’s confused, worried face. “Barbs Dean. Your fucking cock has barbs and they are inside of me.”

That’s not possible, I’m not a cat right now.” Dean replied, and moved again, probably unconsciously, which had Sam lifting his whole upper body to ride the wave of pure pain, followed by a wave of panic, fear of being ripped apart.  
  
Dean stopped moving. “No way. My penis, my human penis, is – “  
  
“Sticking itself into places that barbs should never be, yes.” Sam said. “Just – don’t move.”  
  
Dean was holding himself aloft above Sam; he had been leaning far enough over Sam’s bent body that their faces were close.  
  
“How much pain are you in? What do we do?” Dean asked, slipping right into concerned big brother mode.  
  
“I have no fucking idea. Fuck, this hurts.” For a long moment, Sam felt nothing but intense, overwhelming pain. Then something else began trickling through, one of the barbs was pressing against his prostate. Hard.  
  
“Sam?” Dean asked as Sam began to squirm, and then winced as the movement seemed to dig the barbs in deeper.  
  
It wasn’t that Sam couldn’t handle pain, he had been tortured by the devil himself for years and survived mostly whole, but this was a whole new level of discomfort – pain in his inner walls mixed with mortification and now there was the relentless pleasure of having his prostate pushed against.  
  
It was all too overwhelming. “Please pull out.” He pleaded. He sat up, placed his hands on Dean’s shoulders, bracing himself. “Slowly.”  
  
Dean started to do just that, but the barbs just seemed to dig in deeper, the pain ratcheted. “No, don’t, stop.”  
  
“Okay. Not moving.” Dean’s forehead was pressed against Sam’s. “Don’t worry, we’ll figure this out.”  
  
“You try not worrying with barbs sticking into your ass. Imagine needles piercing your cock.”  
  
Dean shuddered. “Okay, so – should we call Cas maybe?”  
  
“No. No, no, a thousand billion times no.” Sam couldn’t imagine Cas finding them like this. He figured Cas knew, after all this time he had to have heard things, seen things. But having him walk in on them like this, yeah, that was a big fat nope.  
  
“I didn’t think so.” Dean nibbled on Sam’s neck, a tiny bite of a distraction “You get to call the shots here Sam, what do you want to try next?”  
  
“Maybe…” Sam tried to shift, just a little, just to get that damn barb off his prostate but an immediate wave of pain caused Sam to still again. “Maybe if you came your cock would deflate. It’s worth a try.”  
  
“I can’t come on command.” Dean protested, and then, despite the predicament they were in, got that wicked twinkle in his eye. “I’m not you.”

“Fuck you.” Sam automatically responded, but he knew he was blushing. When Dean was being particularly toppy, ordering Sam to come untouched was something he took great delight in. Sam long ago gave up feeling ashamed about the pride he felt by being able to do just that. Even now, despite the pain, between the pressure on his prostate and Dean’s wicked teasing, Sam could feel his cock, which had deflated on entry, slowly begin to fill again. “It’s worth a try, just think – I don’t know – think sexy thoughts and try not to move at all and just come.”  
  
“Sure, no problem. I’ll be perfectly still while I ride out an orgasm, just for you.” Dean closed his eyes; Sam held his breath and – nothing. “Sorry little brother, but if being buried deep inside you for the first time in weeks, with you so tight and feeling so good against my cock, hasn’t made me come, I’m not going to daydream my way into an orgasm. You are far sexier than anything or anyone I could imagine anyway.”  
  
Yeah, his cock was definitely responding to the simulation of the evil prostate piercing barb and the lust-praise of his brother and fuck the pain. “Move.” He ordered. “Just, not too muck okay?”  
  
“Are you sure?” Dean asked, still holding himself up above Sam.  
  
“Just, slowly. And don’t pull out too far, I don’t want them digging in any further.”  
  
Dean was still hesitating, obviously loathe to hurt Sam more.  
  
“It is never going to stop hurting if we don’t push through this. Just move.”  
  
Dean nodded, teeth grazing his lower lip and fuck that was sexy, so Sam kissed him, hard, letting his own teeth nibble on lips that always looked in need of ravishing. Dean was beginning to move, slowly, carefully but fuck, it still hurt and the barb that was pressed against his prostate just seemed to dig in further and red-hot pain warred with white-hot pleasure.  
  
“Not so much.’ Sam broke away from the kiss to request. “Little movements.”  
  
Dean was kind of rocking into him, a short staccato movement that Sam swore he could feel in the pit of his stomach. He fell back against the bed, determined to ride out the waves of pain-pleasure-pain as Dean sat up, carefully pulling Sam’s ass closer to him and fuck, he was so deep inside and the barbs were digging in so tight and Sam was hard and desperate.  
  
He needed Dean to come, so as Dean rocked inside of him, Sam let a hand wander, over Dean’s lower stomach which tightened when Sam’s hand ghosted over his belly button, up his hard abs, to his chest. “Fuck Sam, I’m trying not to lose control here.”  
  
“I trust you.” Sam said, unwisely perhaps but he was overwhelmed by pain and need, and pleasure and Dean and he tweaked one of Dean’s nipples, then pinched the hell out of the other one.

Dean’s damnable barbed cock was jabbing deep inside of Sam and the pain was enough that Sam felt like he was drowning in it. Still, when Dean’s hands moved from the bed to grip Sam’s hips just right, and he could feel Dean shake above him, jostling those barbs in a way that had Sam’s vision begin to white out, Sam orgasmed, untouched, shooting so fast and so hard that he didn’t even notice that Dean had come too, until his mind clicked back on and he realized that the barbs were no longer digging into him.  
  
“Pull out.” Sam gasped. “Quick.”  
  
Dean did, and there was no pain in the wake of his exit. In fact, everything felt kind of numb. A quick check indicated that there was no blood, no obvious injury, nothing seemed torn. Apparently, Dean’s magical barbed cock also came with magically healing come.  
  
After the clean up and the check up, Dean laid beside Sam, both still breathing like runners in mile 28 of a marathon. “So, unless we can figure out a cure for that – problem, I guess no more sex for us.” Dean said, hand finding the one of Sam’s closest to him, fingers interlocking. “At least not that kind of sex anyway.”  
  
“I didn’t say that.” Sam responded, squeezing Dean’s hand. “Next time we’ll be more prepared.”  
  
Dean propped himself on his elbow so that he could look Sam in the face. “Next time?” He asked incredulously.  
  
Sam shrugged. They had been through so much both separately and together, a few little barbs didn’t seem to be that much of an obstacle to overcome. “We’ll figure it out, we always do.”  
  
“Have I told you today how much I love you?” Dean asked, lying back down, turning his body so he faced Sam.  
  
Sam took his free hand, ran his fingers across Dean’s kiss-swollen lips. “I’m kinda of fond of you too.”  
  
When Sam woke up much later, Dean was in cat form, curled against his chest, purring low and deep and Sam wrapped his arms around Dean and let sleep take him right back under.


End file.
